e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Journal of heterocyclic chemistry

A facile and novel synthesis of 1, 6??naphthyridin??2 (1H)??ones

B Singh, GY Lesher

Index: Singh, Baldev; Lesher, George Y. Journal of Heterocyclic Chemistry, 1990 , vol. 27, # 7 p. 2085 - 2091

Full Text: HTML

Citation Number: 31

Abstract

Abstract A new and convenient procedure for the synthesis of 1, 6-naphthyridin-2 (1H)-ones and their derivatives is described. In the first scheme 5-acetyl-6-[2-(dimethylamino) ethenyl]- 1, 2-dihydro-2-oxo-3-pyridinecarbonitrile (4) obtained by the reaction of N, N- dimethylformamide dimethyl acetal with 5-acetyl-1, 2-dihydro-6-methyl-2-oxo-3- pyridinecarbonitrile (3) was cyclized to 1, 2-dihydro-5-methyl-2-oxo-1, 6-naphthyridine-3- ...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

~88%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxylic acid Structure

5-methyl-2-oxo-...

5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile Structure

5-Acetyl-6-meth...

~%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxylic acid Structure

5-methyl-2-oxo-...

5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile Structure

5-acetyl-1,2-di...

~%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxylic acid Structure

5-methyl-2-oxo-...

6-[2-(dimethylamino)ethenyl]-5-propanoyl-1H-pyridin-2-one Structure

6-[2-(dimethyla...

~95%

5-ethyl-1H-1,6-naphthyridin-2-one Structure

5-ethyl-1H-1,6-...

2,4-Hexanedione Structure

2,4-Hexanedione

~%

5-ethyl-1H-1,6-naphthyridin-2-one Structure

5-ethyl-1H-1,6-...

5-amino-4-hexen-3-one Structure

5-amino-4-hexen...

~%

5-ethyl-1H-1,6-naphthyridin-2-one Structure

5-ethyl-1H-1,6-...

6-methyl-5-propanoyl-1H-pyridin-2-one Structure

6-methyl-5-prop...

~%

5-ethyl-1H-1,6-naphthyridin-2-one Structure

5-ethyl-1H-1,6-...

6-(2-(dimethylamino)vinyl)-5-(furan-2-carbonyl)pyridin-2(1H)-one Structure

6-(2-(dimethyla...

~88%

5-(furan-2-yl)-1H-1,6-naphthyridin-2-one Structure

5-(furan-2-yl)-...

1-(2-furyl)-1,3-butanedione Structure

1-(2-furyl)-1,3...

~%

5-(furan-2-yl)-1H-1,6-naphthyridin-2-one Structure

5-(furan-2-yl)-...

3-amino-1-(furan-2-yl)but-2-en-1-one Structure

3-amino-1-(fura...

~%

5-(furan-2-yl)-1H-1,6-naphthyridin-2-one Structure

5-(furan-2-yl)-...

N/A Structure

~%

5-(furan-2-yl)-1H-1,6-naphthyridin-2-one Structure

5-(furan-2-yl)-...

5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile Structure

5-acetyl-1,2-di...

~99%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile Structure

5-Acetyl-6-meth...

~%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

~68%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxamide Structure

5-methyl-2-oxo-...

5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile Structure

5-Acetyl-6-meth...

~%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxamide Structure

5-methyl-2-oxo-...

5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile Structure

5-acetyl-1,2-di...

~%

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxamide Structure

5-methyl-2-oxo-...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxamide Structure

5-methyl-2-oxo-...

~49%

3-amino-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-amino-5-methy...

5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile Structure

5-Acetyl-6-meth...

~%

3-amino-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-amino-5-methy...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

~%

3-amino-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-amino-5-methy...

5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile Structure

5-acetyl-1,2-di...

~%

3-amino-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-amino-5-methy...

Medorinone Structure

~52%

1,6-naphthyridin-2-ol Structure

1,6-naphthyridi...

2,4-Hexanedione Structure

2,4-Hexanedione

~%

6-methyl-5-propanoyl-1H-pyridin-2-one Structure

6-methyl-5-prop...

5-amino-4-hexen-3-one Structure

5-amino-4-hexen...

methylpropiolate Structure

methylpropiolate

~42%

6-methyl-5-propanoyl-1H-pyridin-2-one Structure

6-methyl-5-prop...

2,4-Pentandione Structure

2,4-Pentandione

~96%

Fluoral-P Structure

2-amino-2-hepten-4-one Structure

2-amino-2-hepte...

methylpropiolate Structure

methylpropiolate

~47%

5-butanoyl-6-methyl-1H-pyridin-2-one Structure

5-butanoyl-6-me...

heptane-2,4-dione Structure

heptane-2,4-dione

~%

5-butanoyl-6-methyl-1H-pyridin-2-one Structure

5-butanoyl-6-me...

3-amino-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-amino-5-methy...

~62%

3-hydroxy-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-hydroxy-5-met...

5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile Structure

5-Acetyl-6-meth...

~%

3-hydroxy-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-hydroxy-5-met...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile Structure

5-methyl-2-oxo-...

~%

3-hydroxy-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-hydroxy-5-met...

5-methyl-2-oxo-1H-1,6-naphthyridine-3-carboxamide Structure

5-methyl-2-oxo-...

~%

3-hydroxy-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-hydroxy-5-met...

5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridinecarbonitrile Structure

5-acetyl-1,2-di...

~%

3-hydroxy-5-methyl-1H-1,6-naphthyridin-2-one Structure

3-hydroxy-5-met...